Son of a Sailor
Copyright© 2023 by SmokinDriver
Chapter 29
Coming of Age Sex Story: Chapter 29 - This is a story about a young man that come from a family that made their living on the sea for generations. How does he take what he was born to do and make the most of it. Coming of age, rags to riches. 30 chapters. I hope you enjoy it.
Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa mt/ft Ma/ft Fa/Fa Consensual Rags To Riches Light Bond Anal Sex Masturbation Oral Sex Size
For once I felt alone in a city of millions. I didn’t have anything that I had to do and decided to play tourist for a few days. I walked down and took the subway to Battery park. Walking around with the tourists, I kind of felt like one. I wandered around lower Manhattan and found a bar called the Dead Rabbit. I remembered that my bartender from Audobons used to work there so I stopped in to have lunch and a few drinks. The streets seemed more narrow as if we were stepping back in time before all the cars that needed the room to get around. It was fun to get out and explore.
Grace came back a few weeks later after spending time taking care of her sister. I was back in work mode and she went back to her training. We were getting ready to head out and look at property. But the week before we were going to leave, two things happened. The first was with Grace, she came into the living room and sat in the chair across from me. “Bull, I want to do something but wanted to talk to you first.”
Putting down the book I was reading I looked at her and could tell she was serious. “What is it, Grace?”
“There is a building down by where I workout in the mornings that’s for sale. I want to buy it and rent out the rooms. There are a lot of immigrants and many are women that need a place to live as they work in the laundromats, hotels, spas and restaurants around the city.”
“Can you afford that?”
“You pay me every week and I haven’t been able to spend any of it in the whole time that I’ve worked for you. That and Heather managing my investments have left me with enough to buy the building for cash but I was thinking of putting twenty percent down and financing the rest so that Heather can keep making money for me as the tenants pay off the mortgage for me.”
“Do you want to go to a bank or do you want to borrow from me? I can give you a loan at a better rate. Adam keeps telling me to diversify.”
“I’d like that. Banks don’t treat Chinese women very well.”
She came and climbed on my lap and we cuddled to seal the deal before I took her to bed and we had sex to help her take the edge off of all the excitement she’d pent up inside. The second thing that happened was that Libby Burger’s daughter in law stopped by. Libby’s son Brady had graduated from Yale and was working for his father in the family business. They both had a place in the building. Libby and her husband were on the same floor as me and the son, Brady and his wife Penelope were down closer to the ground floor.
Libby had been cuckolding her husband for years and right in front of her son. Both her husband and Brady knew that they weren’t the most handsome or well endowed men but they had money and security that allowed them to marry up and bring in women that were very pretty. Libby was a trophy wife and Penelope could be on the cover of a fashion magazine and not look out of place. She was one of the prettiest women that I’d ever met and Libby was pushing her to step out and make sure she was taken care of even if Brady was her own son.
The prenups were in place for both of them but the wording didn’t take anything away for cheating. Just from leaving the men they were married to. In fact they were rewarded more if the husband initiated the divorce.
When Grace opened the door to Penelope and let her in, I was surprised but smiled at the beautiful woman and was interested in hearing what she had to say. Libby had introduced me to her when they had first moved to New York after college. Since then I’d seen her a couple times but had never spoken to each other. She came in and I offered her a seat. She was nervous but resolute to say her piece.
We chatted for a while until finally, I said, “Penny, tell me a story.”
She paused for a minute as she got her courage just as Grace came in and set a glass of wine in front of each of us. Penny took a big sip and said, “When I was in college as a freshman, my roommate was a pretty white girl. She lived a few hours from college. One weekend, she drove home to see her boyfriend. He wasn’t expecting her and when she drove up, she saw a car in the parking lot in front of his apartment that she recognized. It was a girl that she’d gone to high school with. She went up and knocked and when he answered and she looked past to see the girl pulling her shirt on, she told her boyfriend to fucking die and she went to get in her car. She didn’t want to go home to her parents. She turned and drove back to school.
“She, like me, grew up with money and when she got tired, she pulled into a hotel to crash for the night. She walked into the hotel bar and ordered a drink. There were a few other people in the bar and they were all men. She ended up in bed with a black guy as she tried to do what she thought about what would hurt her boyfriend the most.”
Penny took a big swig of her wine and continued, “She told me about the size of his cock and how she’d never felt anything like that before in her life and it was amazing. She stayed two nights with him and would have stayed more but he had to head out to his next meeting and she had a class on Monday morning. She said that she was his to use as he wanted. His cock and his fucking were like a drug to her.”
She stopped and looked at me as she finished her wine but I took a sip and didn’t say anything. She set her glass down and looked to the kitchen. Grace came over and filled her glass and after another sip she said, “Libby basically says the same thing and I’ve been afraid that if I did what she told me to, that I would lose my husband and family. I wanted something to make sure that didn’t happen. Brady isn’t the tallest, most muscular, most handsome or anything else but I made a vow to stay with him. I found out a couple days ago that I’m pregnant with his child and that will be the cement that holds us together. I’ve been pushed, hinted to and told that I need to step out and smell the roses and here I am. I want to try what Libby and my roommate Marsha told me that I needed to try. Brady knows that I’m here and is excited to see how it turns out. I don’t understand it but he seems to get off on the idea.”
I didn’t say anything but just nodded. I stood and held out my hand. She stood and took it. I led her to the bedroom and she followed me. When we were in the room, I unbuttoned her blouse and took it off. She had on a white bra and some nice breasts enclosed in it. Next I undid her skirt and then as she stepped out of it, I put it on the chair along with her blouse. She had on shoes, flats and I took those off and put them aside. When she was down to her white bra and white panties, I stood and said, “Undress me.”
She did my shirt and pants as I’d done for her. I wasn’t wearing shoes and was soon down to my boxers. She knelt in front of me and just looked at the lump in my shorts. She gulped, licked her lips then slowly lowered them. The waistband was almost to my knees when the head came into view. I stepped out of my boxers and she blushed.
Standing in front of me I took off the rest of what she had on and laid her back on the bed and spread her legs to lick her to her first orgasm. When she was wet and ready I stepped up and slid into her. She was tight but she opened up to my girth as I slid deeper and deeper. I could feel my pubic bone pressing into her clit as my cock pressed into her cervix. She moaned in pleasure as I did so.
She came on my cock three more times before I filled her with my seed. We were both sweating and as I held my place deep inside of her. She said, “If I’d done that when I first moved in, I’d be having your baby and not my husbands. I’ve never cum when we’ve had sex. Only when he eats me or I play with myself. That was amazing.”
Leaning in, I kissed her. She didn’t want to at first but eventually gave in and started to kiss back like a good slut. My cock stayed hard and I started to fuck her again. This went on a few times and it was a couple hours at least before I slipped out of her. It was followed by a flood of my spend. She just started to cry.
There wasn’t much I could do. Leaning down, I licked and sucked on her nipple. She held my head as she cried. We eventually were laying together with her head on my shoulder. “Bull, I thought I would come up and have sex. Then I would go home and tell my husband, Libby and Marsha that I’d done it once and that was enough. I was wrong. They were all right. I needed this and never had any idea it could be this good. I don’t think I could go without this now that I’ve had it.”
“Some get addicted to alcohol, cocaine or heroin. You’re addicted to me and my cock. You have to be careful as you’ve seen in society. If you let it get away from you, the consequences aren’t good. You married Brady for the money and security for you and your children. If you end up in some house with a bunch of construction workers to meet your cravings it could all end badly and go away.”
“I don’t think I’d ever be that desperate but it’s a good thing to keep in mind.”
“I want you to go home and get in the bathtub and soak for a while. Ask Brady to come in and tell him everything you did and how it made you feel. Today is Thursday. If you and Brady both want this and are okay with it, have him drop you off at my door tomorrow at noon. I’ll bring you home Monday at noon. Every good fucktoy has to be trained and this weekend will begin your training. Also, I fuck a few women and most are private relationships. You, Penny, are a beautiful girl. I’ll be taking you out sometimes, like to the fundraiser Saturday night. Think of yourself as an escort or mistress. It will be clear that we’re together and not just friends.”
Penny looked surprised at the last comment but I said, “I don’t want any false expectations. You will also not be an equal. You will do as I say and you will call me Sir, or Master. As Dickens once said, It was the best of times, it was the worst of times. With great sacrifice comes great rewards and I love to hear a woman orgasm. I want you to go home now and do as you were told. Talk, argue, negotiate and agree with Brady on what your life will look like from today forward. If he kicks you out, I can put you up for a few days but I’m not looking for a girlfriend or wife. I already have one live-in sex slave and don’t need another. Do you understand?”
“Yes, yes Sir. I hope to see you tomorrow at noon. I want this and will do what it takes.”
Grace was in the living room and the door was open. She had heard what was said. She let Penny out and then came in and crawled in next to me to cuddle. “Master, thank you for making me feel special. There are many women that would gladly be your sex slave and if you get more, I would be fine but Penelope is beautiful and it feels like you just turned her down for me and that makes me feel so wonderful.”
“You are special Grace, very special.”
She kissed her way down my body and licked me clean like a good girl. I petted her and eventually fell asleep. She was gone when I woke up. She was at the gym where she worked out and sparred with her martial arts class. There were only four people in the class and they were all very good. The teacher was a master in a few different varieties of martial arts. She also was going to go over some things at her new building.
My own workout was first on my list. Push-ups, sit-ups, burpees and mountain climbers. I didn’t have to leave my bedroom but did have a small workout room with some dumbbells in case I wanted to do some thrusters. I hated thrusters and running but still did both a couple times a week to make sure those muscles got the exercise they needed. I decided that I needed a run and went over to Central Park and ran.
Running gave me some time to think about things and most of the thoughts were good. I could always be a better person but I kind of enjoyed getting the best of others in a deal negotiation or taking advantage of someone that was desperate. Being the dominant one in the bedroom was just natural to me and I didn’t take any classes or try to learn anyone’s style.
After a shower and some eggs. I made some calls to check in on a few things. Grace was home and was only wearing her collar when there was a knock on the door at noon. Grace looked through the peephole and then opened the door for Brady and Penny. She said, “Good afternoon, Brady. It’s good to have you back, Penny.”
Brady said, “Hi Grace. She prefers Penelope.” He looked her up and down but as much as he looked at her naked body, his eyes kept coming back to her collar. They walked in and of course the big view took their attention. I stood and walked over to the entry.
Shaking Brady’s hand I said, “Brady we live in strange times. Did you and Penny come to some agreement? I don’t want to break up any relationship or have to look over my shoulder when I’m out. Penny is a beautiful woman and I enjoyed our time together.”
Looking down at his feet and gaining his resolve he said, “Penelope is my wife and she’s having my child. I think in life you need to know both your strengths and your weaknesses. You need to know what you are great at, what you are good at and what you don’t do very well. I grew up in a home where my mother and father had figured out his weaknesses and they figured out a way to compensate. It was an open marriage but discrete. My father has had mistresses but could never bring them home. My mother has brought home more than a few other men to compensate for my father’s shortcomings. I struggled with it as a child but soon saw that my mother was happy and she and my father are still together even though most of my friends’ parents have split up to find a solution to their partner’s shortcomings.”
“I hope that Penny is happy and well taken care of. I know she’s pregnant with your child and like I said, I hope you have a long and happy marriage with your wife. You’re also giving a part of her to me. I’m not a guy just out to get laid. That would take a few seconds and a snap of my fingers. I’m a dominant lover and use women to make me happy. Your wife will be one of the women that I use. I’ll keep her safe and bring her home when I’m done.”
“A happy wife is a happy life. I’m sure there will be struggles at times but I know what I’m getting into. She said that you were going to take her for the weekend and maybe take her out in public. That’s a big step but we want to see where this goes and I’m willing to trust her. I’ll see her on Monday.”
Grace opened the door and he kissed Penny one last time before walking out. The door closed behind him and all attention turned to Penny. “Penny, how did last night go?”
“He called in sick today so we could finish our talks or rules. Brady kept wanting to limit what you could or couldn’t do. I told him that when I was with you that the only rule was stop or yes sir. I know that if I said stop it wouldn’t just be for a minute but forever. I told him that you owned my body and soul when we were together. If he couldn’t agree to that then I would get a dildo and live a miserable life as his wife.”
“He didn’t seem to be too demanding when he dropped you off. Did he finally agree?”
“Brady said he was going to make a few demands when he dropped me off. Man to man. I think when he saw Grace wearing only her collar, trying to ask for me to be treated any differently would have been pointless so he caved and just accepted your terms.”
She had a bag with her and a dress. I asked, “Why did you bring clothes? Did I tell you to?”
“I wasn’t sure about the event tomorrow and didn’t want to have to go home for clothes so I brought some just in case.”
“Good girl. I was using the event as an example. I wasn’t planning on going to a fundraiser this week. Come sit down so we can talk about some real rules.”
She walked into the living room and sat down. I said, “You were right about obeying me or ending the relationship. We’ll have a safe word. This is if you want to stop. If you say the word, ‘Elephant’ and it’s out of context, everything will stop and I’ll check to see if you are alright. Then we’ll discuss why you said it and what will happen next. You can also say yellow and that lets me know that you are getting close to your limits. I’ll decide what to do then. Is that fair?”
“I understand. Yellow and elephant are my two ways to tell you that I’m not comfortable.”
“I hope to make you uncomfortable a lot but those mean that you are at a point you feel unsafe or may want out.”
“Yes, Sir.”
“I would normally have you get naked now but we’re going out. Give me your ID and I’ll carry it for you. You won’t need anything else.”
“Where are we going?”
“Wherever I want.”
“Um, okay.”
Grace got dressed and went down to get the car and I helped Penny put her bags in my room and get her ID. Grace and I had discussed our day before Penny had arrived so after we were in the back of the Rolls, Grace just drove. We went to a nice dinner at a restaurant that I wasn’t a part of. It was interesting to watch both girls and how they acted.
It reminded me of the first time I walked around with a backpack full of cash. I felt like everyone was out to steal it. When I walk around with a backpack with a change of clothes and a towel, I don’t think twice about it. I’m sure that Penny felt like everyone in the restaurant knew that she was out cheating on her husband just to get some big cock that she craved but in reality, she was just another girl having dinner with some friends. She was young and beautiful so she was always looked at a little more often but for a different reason.
We talked about Penny and her life in college and after. She’d met her husband at a sorority social and before she even walked in the door, she knew who he was, who his family was and how much money he was or would be worth. As she got to know him, she fell in love with him and wasn’t a total gold digger but it was something that opened the door for her to even give him the time of day. She was popular in high school but her parents put a high value on good grades and being up to the standards of a high society girl. She didn’t sleep around much in high school or before meeting Brady. She had one steady boyfriend in high school that she’d slept with on prom night and a couple times after that.
Grace said, “I didn’t have to worry about high school boys. It was my family and teachers that kept them away and kept me and my sister for themselves. I learned how to fight but it wasn’t something I would try to do since by then I was too far down that path. Now I belong to Bull and no one even tries to mess with me. My collars let them know that I’m not available.”
After dinner we went to the sex club and when I explained where we were, Penny got very nervous. I said, “This is where I met your mother in law. She and your father inlaw might be in there now. They may have brought Brady to get his mind off of you being with me. I’ll let you wear a collar so that everyone knows that you are not to be touched.”
In the locker room we were changing and she was nervous but did as she was told. She and Grace were both beautiful but Penny was gorgeous. Her age and beauty had many men and women following to either watch or have a chance of being with her. She got a couple swats on her ass as she looked at the ground. I wanted her to have her head up and look them in the eye. This is who she was and she should be proud of it and not ashamed.
When the first man looked down and away, it gave her more confidence and soon she was right up there with Grace as her attitude changed to one of privilege and not of shame. Grace whispered to Penny, “You’re beautiful, young, smart and have a big hard cock that loves to fuck you. Every man and woman in this place wishes that they were you or could be with you. Act like the queen that you are. We only answer to our king, not the riff raff.”
Penny thought a little about that but soon came around. We didn’t go to the dungeon but up to one of the rooms. She was happy to have my cock and soon didn’t even care that others saw her sucking and fucking like a size whore that she was. It was a little bit of a surprise when she had a strange woman eating my seed out of her pussy when I pulled back but there were a lot of women that would be honored to get a taste of her pussy.
As we rode home afterwards, Penny looked like she was deep in thought. I asked what was going on between her ears and she said, “I’m still very new to this dominant submissive thing. With you, there’s really only one place for me. I can either submit or not be with you. For everyone else it feels like I’m on the other side of the equation. Brady does what I say. Both men and women look down or away if I look into their eyes. I love the feeling of power that I have but also love when I know that you picked me to be one of your women to play with and use.”
“When two people get together they have to figure it out on a personal level. This is true in sex, business, and family. I defer to my parents out of respect. The same is true for my aunts and uncles. My cousin, she would be the one to answer to me. In business, even my uncles will defer to me. There is no one mold for every relationship. Did you enjoy being the one that is in charge or do you enjoy being below me more?”
“That’s a trick question. I think that some of the power that I feel and enjoy comes from being with you. It feels like there is a hush of respect wherever you go.”
Then it was my turn to stop and think for a bit and the rest of the ride home was quiet. Both women slept with me and then cleaned each other up in a 69. Penny wasn’t as enthusiastic but went along with it and was pleased with her performance when we all cuddled up and went to sleep.
Saturday, I got up and did my workout and ran. I didn’t have fun running but the cardio and being out in the park felt good. When I made it back to the condo dripping in sweat, both Grace and Penny were awake and having tea. When I walked in, Grace stood so that she would be ready to serve me by getting me a drink or helping me get clean. Penny saw that she was slow but was soon standing beside Grace. Both just wore a collar. It was sexy as hell but I told them to relax and that I was going to shower.
When I’d cooled off and was clean, I put on a pair of jeans and a t-shirt and went out to get some coffee. Penny waited for me to sit with them and she asked, “So what are the plans for today?”
“Penny, I’m glad that you’re here but even at my young age, I can’t fuck 24 hours a day and I do have a life beyond my bedroom. I was going to stop by some of my restaurants and see how things are going, I need to get my sailboat out on the water at some point and it’s a pretty day. I think I saw that there was going to be an art festival this weekend in Battery Park. Other than that, I have no plans. Did you need some cock to start your day?”
“I’d love some.”
When someone is so forward to ask for cock, it is a good thing to give it to them. I stood and bent her over the couch before lowering my pants and filling her. I pulled her hair and told her what good slut she was while I plowed her from behind. When we were done we all got dressed and went over to the yacht club. I’d found a nice catamaran that had a center living and sleeping area. The boat was almost 60’ long but had self-furling sails. Auto-pilot and a top of the line navigation system allowed for me to sail her by myself if I needed to but with Grace and Penny there to help with the lines it was easier to cast off and tie up at the dock. We motored south until the river widened and the boat traffic was more spread out before we switched from motors to sails.
The sun and wind were both great and the girls were all smiles as we sailed around the upper bay and the Statue of Liberty. It was late in the afternoon when we tied up and went into the yacht club for drinks and dinner. The girls were all smiles and had a nice bit of sun from being on the water. A few people stopped by to say hello and a couple to talk about the cat. They had seen us out on the water and said that it looked like fun as fast as we were going.
We spent the evening and night back at the apartment fucking like bunnies and training Penny that women can be fun too. She learned to eat pussy and got used to Grace being between her legs as well. It was a good day. Sunday we walked around the art festival and just enjoyed being out. We stopped by Dante’s for brunch and some drinks. It was soon time to call it a day and went back to the apartment. The afternoon was spent having a massage, a sauna and a shower before we went into the private lounge and had some drinks.
Penny commented, “I think I’m getting over some of my shyness. In the sauna, I didn’t think twice as other people came in and saw me naked and sitting on a towel. I would give them the once over and they would look at me but it was as if we were just meeting on the street and weren’t completely naked.”
“On the street someone might have on some stylish sunglasses, shoes or a hat. It may make you look twice like they do when they see your gorgeous body but when you boil it down, it is just a hat, some glasses or shoes. Boobs, pussy, cock, we all have them and they just come in different shapes and sizes. You get used to them. I know your pussy is getting used to being filled with my cock.”
“I didn’t think it would fit the first time I saw it hard but now I know how well it fits and my pussy gets wet like my mouth waters for a chocolate chip cookie.”
It was another night of sex but then it was Monday and she was getting ready to go home. I said, “It was a fun weekend and you were a fun girl. Grace and I have a lot of traveling to do. I’ll try to let you know when we’re back in town for a while.”
Penny stepped into my arms and gave me a hug. “I had a great weekend. It made me see what I have in my husband. Someone that isn’t running off for weeks or months at a time. Someone that’s there for me. I also see what is out there and can find if I’m willing to look hard enough. I’ve tasted the forbidden fruit and it was good. Let me know when you’re back in town. If you’re gone too long, I may need to hop on a plane and find you.”
With that, I got a kiss and didn’t let her get away with a peck on the lips but a five minute make out session that had her wanting to go back into the bedroom before I turned her to the door and patted her ass as she headed for the elevator with her overnight bag in her hand.
As I sat on the couch I said to Grace. “I think we should spend the week getting things in order here and then go visit all the properties and see how things are running. We do have to be hands-on managers to keep our tax status.”
“I’ll be ready. I only have one building and it’s doing fine. How long do you think we’ll be gone so I can let Wang know?”
“Not more than a month or two. I need to make time for things and I seem to be pushing myself for the sake of pushing. Not because I need to. I plan to see our properties, then maybe take the boat south either to park it for the winter or keep going and sail anywhere in the world.”
“Is your boat big enough to go across the Atlantic or around the world?”
“Sure. Bigger storms would be something we would want to avoid but that’s true on almost any boat. There’s more than enough storage for supplies and we have enough fuel to keep us going without a lot of wind or to run the generator to charge the batteries and run the lights.”
“That sounds both fun and scary.”
“Like the first time I fucked your ass?”
“Like every time you fuck my ass. Just like Penny I’m always afraid that it won’t fit.”
For the next week, I worked with my CPA, with Gary that manages all the restaurants and clubs. I stopped by the bank and found two properties that were in line with what I was buying. I signed a contract but wouldn’t close until I was back from my trip. Grace and I flew to Florida and she went to see her sister and I went to stay with Darren, Casey and Kat.
One morning I was doing my pushups and Kat walked in and started to do some yoga poses. I asked what she was doing and she said, “Bull, I play soccer and do gymnastics but when I move away to college I won’t be doing either of those. I heard some of my mom’s friends talking and they all said that yoga kept them flexible and strong. I got a book at the library and started. Just like you work out everyday, I’m going to do yoga. I’ve already started to do some of the poses that are for advanced people. I want to be in shape like you. My dad is starting to get a pot belly and Mom has to nag him all the time about how he needs to stay in shape.”
“Then be the best yoga person there is. You can teach me when I’m in town.”
I learned up dog, down dog and tree pose after I’d completed my workout. It was good to see her each morning and night. Casey was good to see as well and since Kat was getting older and not napping I had to stay until she’d gone to school to spend time with Casey. But we didn’t spend all day together. I was in town to work and see family.
During the day, I’d visit with my cousin, my uncles and the properties. Amy and I spent a few days together as we reviewed all of the timeshare properties. After we had talked about each property and the sales, management and profits, she said, “Bull, we are out in the front of this wave. There are others trying to copy us but we’re always the first one in most places and doing things that others are in a hurry to copy to try to catch up. I think that we have the lock on the city Locations because of the business concepts that we have. Others try to just go after individuals or families and have a hard time or have to go so cheap that they don’t make money. A few have come to me to see if we’re interested in buying. I let them hold the property and the losses. I’m not bailing them out.”
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